SYNTHESIS: Apiole, as the crystalline essential oil
1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, is isolated directly
from commercial Oil of Parsley, by careful fractional distillation.
It is the fraction that boils at 165-167 °C at 27 mm/Hg. A solution
of 19.8 g apiole in a mixture of 43 g KOH and 60 mL hot EtOH was
heated in the steam bath for 24 h. With vigorous stirring, it was
diluted with H2O, at a rate which the crystals that formed
spontaneously could accumulate from the turbidity that was generated.
When no more H2O could be added (there was persistent oiling out of
material) the reaction mixture was filtered to give 12.1 g of an amber
solid material. This was recrystallized from 20 mL boiling hexane,
which was filtered while hot to remove insolubles. From the cooled
filtrate, there was obtained 9.3 g of
2,5-dimethoxy-3,4-methylenedioxy-1-propenylbenzene, isoapiole, as pale
cream-colored solids.

QUALITATIVE COMMENTS: (with 25 mg) The intoxication was there at an
hour and a quarter, and I was hit with nausea with no particular
warning. I am shaky, a little dilated in the eyes, and there is a
modest depersonalization (reminding me of LSD). Time might be
slightly slowed, and there is a mild ataxia in the legs. A couple of
hours later, all effects are going away fast. I ate an apple, but
maybe my mouth didn't work quite right. The apple was incredibly
noisy.

(with 32 mg) I am up to a 2 1/2 plus at something after two hours,
with no apparent visuals, no push, no erotic. And a few hours later
it is quietly slipping away. It felt completely safe, and without any
conspicuous psychedelic action, at least at this level.

(with 50 mg) I took graded doses of 10 milligrams every thirty
minutes for a total of 50 milligrams, and there were no effects at
all.

(with 50 mg) In the middle of this all, I found myself getting into
abstract thinking, and maybe some imagery as well. The effects were
disappointingly light.

(with 75 mg) This was equal to somewhere between 75 and 100
micrograms of LSD. I was caught up with the imagery, and there was an
overriding religious aspect to the day. The experience had an
esthetic value. I liked it.

EXTENSIONS AND COMMENTARY: DMMDA was the first of the tetraoxygenated
amphetamine derivatives that was ever explored in man, back in 1962.
And it is not easy to find an acceptable single phrase to describe its
action or an acceptable number to describe its potency. I have put
the value of 10 mescaline units (M.U.) into the literature and this
would imply that maybe 30 milligrams was an active dose. This is
probably too low, and some day I would like to run an experiment with
the entire research group with this compound to see just what it
really does.

The essential oil that corresponds to DMMDA is, of course, apiole from
the Oil of Parsley, which again ties together the spice world and the
amphetamine world. And there is isoapiole, also a natural thing.
This pair represents the ring-substitution pattern of one of the ten
essential oils and DMMDA is one of the ten essential amphetamines.